Revenue Builders Podcast Summary

Episode: Best Practices from Elite Sales Leaders
Date: July 6, 2023
Hosts: John McMahon & John Kaplan
Guests: Mark Roberge (HubSpot, Stage 2 Capital), Chris Degnan (Snowflake), Cedric Pesh (MongoDB)

Overview

This episode curates practical, hard-won wisdom from top Chief Revenue Officers about what it really takes to build and scale high-performing sales teams. The hosts dive deep into the realities of being the first sales hire at a startup, the critical importance of hiring, the role of purpose in sales teams, retaining top performers, and why meticulous execution matters. Through vivid stories and candid advice, listeners get actionable takeaways and a behind-the-scenes look at the journeys of elite CROs.

Key Discussion Points and Insights

1. The Raw Realities of the First Sales Hire

Mark Roberge (HubSpot)

• CRO titles at a tiny startup are "kind of a joke" – you do everything, from sales to building dashboards. (02:25)
• The first sales hire functions as both a product manager and sales rep, gathering market feedback and creating early success stories.
• The importance of setting up scalable systems and processes—even as a solo contributor—to define future culture.

Notable Quote:

“I personally don’t think pricing matters a lot right there. I think you’re just trying to get people in and create success stories and you’re trying to get good market learnings back to the product team.”
— Mark Roberge (03:45)

• Hiring Focus: When shifting from solo sales to building a team, prioritize hiring A+ players over perfecting onboarding or management processes, because great people outperform imperfect systems. (05:30)

2. Developing Sales Managers from Within

Mark Roberge (HubSpot)

• High quota attainment for internally promoted managers; process included hitting quota, "leadership school," and coaching a peer before leading a team. (06:21)
• The system is intended to filter for those truly committed and suitable for management, not just the top-performing rep.
• Downside: Few external hires — creates a strong culture but limits outside perspectives.

Notable Quote:

“The job of salesperson and manager is so different… So I put together a process: step number one, hit your quota six months in a row... then you go into leadership school, then you coach a new hire for three months alongside your quota.”
— Mark Roberge (07:32)

3. Hiring for Context, Not the Resume

Mark Roberge (HubSpot)

• Hiring must fit the context: what you sell, who you sell to, stage and culture of your company, and geographic markets. No "universal top sales rep" profile.
• Success traits in one company may not translate to another due to differences in brand, market, and sales process.

Notable Quote:

“There is no universal top sales hire profile. It’s very contextual to your go-to-market context… So hiring is one of those.”
— Mark Roberge (10:43)

• Creating hiring scorecards: List attributes from analysis of current team (e.g., coachability, work ethic, curiosity), then define what “high, medium, low” scores look like for each. (12:00)

4. Startup Realities & Competing with Giants

Chris Degnan (Snowflake)

• Early discomfort: “This is the biggest mistake of my life,” as the solo sales hire at Snowflake, sitting among engineers (13:56)
• Role was largely about generating customer feedback, holding himself accountable for “eight calls a week,” and sending weekly activity updates to the entire team and board (15:00)
• Emotional and financial grind: No commissions for ~2.5 years, major pay cut, while competing with Amazon and Teradata.
• Early strategy: Target Amazon Redshift customers unhappy with product quality; later pivot to “end-of-life” Netezza customers; Teradata fell behind by underestimating the cloud. (17:46)

Notable Quote:

“There’s a misperception… you can go into an early-stage startup and make a ton of money. I will tell you, my wife was pretty pissed at me for two years because I had no commissions coming in.”
— Chris Degnan (18:10)

5. Three Drivers for Success

Chris Degnan (Snowflake)
Describes his core motivations:

1. Overwhelming fear of failure
2. Mentality of always having to earn your job
3. Openness to feedback and learning
   Personal story of humble beginnings to high achievement, emphasizing resilience and adaptability. (22:06)

6. Balancing SMB and Enterprise Sales Motions

Chris Degnan (Snowflake)

• Warns against “starry eyed” focus solely on enterprise deals; business needs both high-velocity SMB wins and unpredictably large enterprise sales.
• New customer logos, not just large deals, are key to sustainable growth. (25:08)

Notable Quote:

“The large enterprise is wonderful, but they’ll surprise you in the upside one quarter and they’ll surprise you on the downside the next quarter. If you build a business just on the large enterprise, you’re screwed.”
— Chris Degnan (25:29)

7. The Power of Purpose for Sales Teams

Cedric Pesh (MongoDB)

• Leaders and teams must introspect to define “why are we doing this?”—especially important during tough times, like COVID.
• Strong execution isn’t enough; a compelling, collective vision inspires greater commitment and resilience. (27:06)

Notable Quote:

“If it’s only about the paycheck, the team starts saying, I can’t take that. It’s too hard, at least if you pretend to excel... There is this whole process of working together to come up... I have a dream. Let’s define that dream. Let’s see if this is authentic, it’s us or it’s someone else’s dream.”
— Cedric Pesh (30:22)

• Memorable analogy: Don’t just “assign tasks,” inspire longing for “the endless immensity of the sea.” (32:00)

8. Deep Care and Retaining Top People

Cedric Pesh (MongoDB)

• Story: As a young French rep in Italy, nearly quit due to hardship; his manager, Carlo, noticed immediately and helped him find a place to live, even personally loaning money until Cedric could pay it back from commissions. (34:04)
• This act of authentic care prevented his resignation and built lifelong loyalty.

Notable Quote:

“This guy believes in me more than I believe in myself… I can’t give up on this guy. I can’t quit on this guy.”
— Cedric Pesh (36:01)

• Great leaders demonstrate genuine interest in their team’s lives; “We are in the people business, not the software business.”

9. Long-Term Sales Craft and Dealing with Different Leaders

Cedric Pesh (MongoDB)

• Advice to young salespeople: Be patient, focus on your craft, resist chasing short-term promotions or rewards. Sales success is a long-term game. (38:00)
• Three kinds of leaders:
  • Great: Inspire and worthy of imitation
  • Average: Don’t add or subtract value; learn to “use them”
  • Bad: Provide a clear example of what never to do

Notable Quote:

“Your ambition is to be amazing at what you do in the long term. You’re not going to win or lose in the next couple quarters, you’re going to win in the next 20 years.”
— Cedric Pesh (38:40)

10. The Crucial Importance of Execution Details

Cedric Pesh (MongoDB)

• Using his background as a downhill ski racer to illustrate: ‘Water boils at 100 degrees, not 98; those last two degrees are crucial.’
• Many sales processes are dismissed as failures due to poor execution—not the design itself. (42:08)

Notable Quote:

“Between 98 degrees where water doesn’t boil and 100 degrees, there is a difference. And those two degrees are actually incredibly important… Greatness in sales requires a lot of curiosity and curiosity has to do with details.”
— Cedric Pesh (42:20)

Notable Quotes & Memorable Moments

• [02:25] Mark Roberge: “Titles don’t tell me much when I’m talking to other folks…at that stage…my title was VP of sales, but I was salesperson.”
• [07:32] Mark Roberge explains the manager development process: “Step number one, hit your quota six months in a row…leadership school…coach a new hire for three months.”
• [18:10] Chris Degnan: “My wife was pretty pissed at me for two years because I had no commissions coming in.”
• [25:29] Chris Degnan: “If you build a business just on the large enterprise, you’re screwed.”
• [30:22] Cedric Pesh: “If it’s only about the paycheck…there is a moment where [they say] I can’t take that. It’s too hard.”
• [32:00] Cedric Pesh: “If you want to build a ship, don’t drum up people to collect wood…teach them to long for the endless immensity of the sea.”
• [36:01] Cedric Pesh: “This guy believes in me more than I believe in myself…”
• [38:40] Cedric Pesh on long-term focus: “You’re not going to win or lose in the next couple quarters, you’re going to win in the next 20 years.”
• [42:20] Cedric Pesh: “Water boils at 100 degrees, not 98…those two degrees are incredibly important.”

Timestamps for Important Segments

• First Sales Hire Challenges: 02:25–06:09 (Mark Roberge)
• Building First-Line Sales Managers Internally: 06:21–09:34 (Mark Roberge)
• Contextual Hiring: 09:58–13:31 (Mark Roberge)
• Startup Sales Reality & Competition: 13:56–21:44 (Chris Degnan)
• Overcoming Fear, Earning Your Job: 22:06–24:57 (Chris Degnan)
• Balancing SMB and Enterprise Sales: 25:08–26:25 (Chris Degnan)
• Purpose and Motivation in Sales Teams: 26:58–33:13 (Cedric Pesh)
• Manager’s Act of Caring: 34:04–37:37 (Cedric Pesh)
• Advice for Young Salespeople: 38:00–41:04 (Cedric Pesh)
• Importance of the Details: 42:08–43:05 (Cedric Pesh)

Conclusion

This episode delivers raw insights from leaders who've built sales machines from zero at breakout tech companies. Listeners are encouraged to focus on hiring for potential, develop leaders internally, inspire teams with meaningful vision, pay close attention to execution, and measure their careers not by their last quarter, but over decades. Human care and curiosity, not just process and numbers, are the secret ingredients to enduring sales success.